Lewis acid-catalyzed Diels-Alder reaction of 2-cyclopentenones with Danishefsky's diene: double bond isomerization of tetrahydro-1H-indene-1,5(7aH)-diones, and attempts on an asymmetric catalysis

2011 ARKIVOC  
This work describes the investigation of the Diels-Alder reaction of the electron-rich diene trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky′s diene) and the non-activated dienophiles 2-cyclopentenone and 2-methyl-2-cyclopentenone with respect to reactivity, regioselectivity and stereoselectivity. An observed double bond isomerization limits the practicability of 2-cyclopentenone as a dienophile in Diels-Alder reactions. 2-Methyl-2cylopentenone could be converted quantitatively
more » ... to one regioisomeric Diels-Alder adduct, however the stereochemical control turned out to be very demanding.
doi:10.3998/ark.5550190.0013.302 fatcat:k6gcm4b5ivbq3csfw2nrdhu5du